M. Samoto, M. Nagano, Yoko Suzuki
Oct 15, 1995
Citations
0
Influential Citations
6
Citations
Journal
Chemical & Pharmaceutical Bulletin
Abstract
Diels-Alder reactions of ethyl (E)-3-(1,3-benzothiazoI-2-yl)-3-cyanopropenoate (2) as a 1-aza-1,3-butadiene are described. The diene (2), bearing electron-withdrawing ester group, reacts with electron-rich dienophiles (3a-d) under extremely mild conditions to give corresponding cycloadducts (4a-d) in high yields with high regio- and endo-selectivities. Treatment of 2 with electron-donating allyl alcohols (5a,b) causes tandem transesterification and intramolecular cycloaddition to afford cis-fused polycyclic systems (6a,b) in one step